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Our top choices for Fleming Key hotels

A swimming pool with lounge chairs and palm trees.
A bar area with a wooden counter, bar stools, and a sign that reads 'So we BEATON.'
A modern living room with a sectional sofa, a small round table, and a potted plant.
Sports facility

1. Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection
New Town
United States
Eli
CA $175
CA $237 total
includes taxes & fees
Oct 25 - Oct 26
Hilton Garden Inn Key West / The Keys Collection
A pool area with lounge chairs and umbrellas, surrounded by palm trees.
A modern office space with a reception desk, computer, and seating area.
A hotel room with a large bed, a wooden nightstand, a desk, a chair, and a window with curtains.
A wooden outdoor dining table set with glassware, candles, and lanterns, surrounded by lush greenery.

2. Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Fairfield by Marriott Inn & Suites Key West at The Keys Collection
New Town
United States
Brian
CA $199
CA $264 total
includes taxes & fees
Oct 14 - Oct 15
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.
A hotel room with a large bed, a TV mounted on a wooden cabinet, and a balcony with a view of palm trees.
A modern kitchen with a marble island, wooden cabinets, and pendant lighting.
A hotel room with a balcony, a bed, a desk, and two chairs.

3. Hampton Inn Key West FL

Hampton Inn Key West FL
Key West
United States
Andrew
CA $241
CA $272 total
includes taxes & fees
Oct 25 - Oct 26
Hampton Inn Key West FL
A building with a white exterior, a large red awning, and a gated entrance.
A paved pathway lined with various plants and trees, leading to a building with a beige exterior.
A pool area with lounge chairs and a lifebuoy.
A small, enclosed porch with a chair and a table, surrounded by lush greenery and a white lattice fence.

4. Authors of Key West Guest House

Authors of Key West Guest House
Key West Historic District
United States
Robbie
CA $178
CA $201 total
includes taxes & fees
Oct 14 - Oct 15
Authors of Key West Guest House
A hotel room with a bed, a view of the beach, a hammock, and beach chairs.
A pool area with blue lounge chairs, a hot tub, and a covered seating area.
A marina with boats docked, a beach resort building, and palm trees.
A beachfront hotel with multiple colorful buildings, a pool area, and a boat dock.

5. Ibis Bay Beach Resort

Ibis Bay Beach Resort
Northside Resort
United States
Andre
CA $159
CA $225 total
includes taxes & fees
Oct 14 - Oct 15
Ibis Bay Beach Resort
A swimming pool with water splashing, surrounded by palm trees and a building in the background.
A two-story yellow house with a porch, white railings, and green shutters.
The exterior of the Silver Palms Inn with a two-story structure, a green awning over the entrance, and a palm tree to the right.
A hotel with a pool, bicycles, and lush greenery.

6. Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West
United States
sam
CA $127
CA $239 total
includes taxes & fees
Oct 25 - Oct 26
Silver Palms Inn & Historic Homes
Pool
A spacious living area with a sofa, chairs, a coffee table, and a foosball table. Large windows offer a view of the outdoor area.
A couple holding hands in a tropical setting with palm trees and greenery.
A modern cafe with a wooden counter, seating area, and shelves stocked with beverages.

7. Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
New Town
United States
Esteban
CA $166
CA $267 total
includes taxes & fees
Oct 14 - Oct 15
Blue Flamingo Resort Key West
A balcony with a view of a pool area, palm trees, and outdoor seating.
A sign for Doubletree by Hilton Grand Key Resort surrounded by lush greenery and palm trees.
A hotel room with a bed, a desk, a chair, a balcony with a view, and a ceiling fan.
A conference room with a patterned carpet, multiple tables, chairs, and two chandeliers.

8. DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
Key West
United States
Nancy
CA $182
CA $253 total
includes taxes & fees
Oct 27 - Oct 28
DoubleTree Resort by Hilton Grand Key - Key West
A wooden archway leading to a pool area surrounded by lush tropical vegetation.
A tall palm tree with a white building in the background.
A large, two-story building with a symmetrical facade, a central entrance with a double door, and a balcony on the upper floor.
A beach with palm trees, a sandy shore, and a calm sea under a clear sky.

9. Parrot Key Hotel & Villas

Parrot Key Hotel & Villas
Northside Resort
United States
Anthony
CA $181
CA $286 total
includes taxes & fees
Oct 14 - Oct 15
Parrot Key Hotel & Villas
A marina with boats docked, a pool area, and a building with a white facade.
A covered outdoor seating area with tables and chairs, overlooking a marina with boats.
A clear view of turquoise ocean water and a blue sky with clouds.
A breakfast setting with a table, chairs, a vase with flowers, and a city view.

10. Hilton Key West Resort & Marina

Hilton Key West Resort & Marina
Stock Island
United States
Eric A
CA $186
CA $293 total
includes taxes & fees
Oct 26 - Oct 27
Hilton Key West Resort & Marina
A balcony with wicker furniture, a view of the sea, and a spiral staircase.
A modern dining area with a glass table, four chairs, and a ceiling fan.
A swimming pool with lounge chairs and palm trees, overlooking a sunset over the water.
A spacious lobby with a marble floor, leather sofas, and large potted plants.

11. Beachside Resort & Residences

Beachside Resort & Residences
Key West
United States
Brenna
CA $167
CA $324 total
includes taxes & fees
Oct 29 - Oct 30
Beachside Resort & Residences
A beach with a wooden pier, palm trees, and beach umbrellas.
A modern bar area with a central island, white bar stools, and a view of the ocean.
An outdoor dining area with tables set for guests, overlooking a calm sea and a pier.
An outdoor dining area with tables and chairs, overlooking the ocean.

12. The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton
Old Town Key West
United States
Darlene
CA $229
CA $355 total
includes taxes & fees
Oct 27 - Oct 28
The Reach Key West, Curio Collection by Hilton
A bottle of Marc's Reserve 12 FL. OZ. on a coaster with a metal table.
A pool with a lion head sculpture in the center.
A potted yellow orchid plant in a garden setting with a brick pathway, palm trees, and a white building in the background.
A front door with purple shutters, a small porch, and a doormat with 'The Artist House Circa 1890' text.

13. Artist House Key West

Artist House Key West
Key West Historic District
United States
Debbie
CA $298
CA $336 total
includes taxes & fees
Oct 29 - Oct 30
Artist House Key West
A wooden boardwalk with a palm tree and lamp post, leading to a waterfront.
A hotel room with a desk, two beds, a TV, a ceiling fan, and a balcony with curtains.
A pool area with lounge chairs, palm trees, and a building with a tiled roof.
A modern restaurant with a wooden counter, seating area, and large windows.

14. Courtyard by Marriott Key West Waterfront

Courtyard by Marriott Key West Waterfront
Northside Resort
United States
Everton
CA $262
CA $295 total
includes taxes & fees
Oct 26 - Oct 27
Courtyard by Marriott Key West Waterfront
A wooden deck with wicker furniture and a glass balustrade overlooking a beach.
A resort with a pool leading to a beach, surrounded by palm trees and white buildings.
A beach with white lounge chairs and umbrellas, a sandy shore, and a calm sea under a partly cloudy sky.
A beachside spa with two massage tables under a canopy, overlooking the sea and a pier.

15. Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton
Old Town Key West
United States
Rita
CA $308
CA $443 total
includes taxes & fees
Oct 25 - Oct 26
Casa Marina Key West, Curio Collection by Hilton
A narrow outdoor pathway flanked by potted plants and a wooden staircase leading to a white door with shutters.
A bedroom with a bed, nightstand, lamp, air conditioning unit, and a no smoking sign.
A two-story building with a porch, a sign reading "The Grand Guesthouse," and a purple flag.
A covered outdoor area with a wooden staircase, seating, and potted plants.

16. The Grand Guesthouse

The Grand Guesthouse
Old Town Key West
United States
Justyn
CA $171
CA $228 total
includes taxes & fees
Oct 14 - Oct 15
The Grand Guesthouse
A dining table with plates of food, a drink, and a view of a pool and palm trees.
A hotel room with a bed, a TV, a coffee table, a sofa, and a view of the ocean.
A person standing by a window overlooking a beach with palm trees and the ocean.
A hotel entrance with a palm tree-lined driveway, a vintage car, and a metal canopy structure.

17. Margaritaville Beach House Key West

Margaritaville Beach House Key West
Key West
United States
Richard
CA $298
CA $425 total
includes taxes & fees
Oct 19 - Oct 20
Margaritaville Beach House Key West
A large, ornate hotel with a pool, palm trees, and a view of the ocean.
A large, two-story house with a prominent tower and a covered porch.
A gated entrance with a blue metal gate, palm trees, and a building with a red roof in the background.
A balcony with white railings and a table, overlooking a beach with palm trees and a clear blue sky.

18. Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive
Old Town Key West
United States
Amy
CA $199
CA $404 total
includes taxes & fees
Oct 26 - Oct 27
Southernmost House - Adult Exclusive
A wooden deck with wicker furniture, a white staircase, and a lush garden area.
A hotel entrance with a sign reading "Heron House Office."
A two-story house with a balcony, surrounded by palm trees and a clear blue sky.
A hotel room with a large bed, a view of a swimming pool, and a balcony with outdoor seating.

19. Heron House - Adult Only

Heron House - Adult Only
Old Town Key West
United States
Amanda
CA $172
CA $241 total
includes taxes & fees
Oct 14 - Oct 15
Heron House - Adult Only
A large, white, two-story building with a balcony and a sign reading "The Marker Resort."
A marina with various boats docked, including a green and white boat named 'Jolly Roger'.
A resort with a swimming pool, lounge chairs, umbrellas, and palm trees.
A covered outdoor area with a pool, palm trees, and lounge chairs.

20. The Marker Key West Harbor Resort

The Marker Key West Harbor Resort
Key West Historic District
United States
Lynne
CA $279
CA $404 total
includes taxes & fees
Oct 25 - Oct 26
The Marker Key West Harbor Resort
View all properties

Hotels recommended for families in Fleming Key

A pool area with lounge chairs and umbrellas, surrounded by palm trees.
A modern office space with a reception desk, computer, and seating area.
A hotel room with a large bed, a wooden nightstand, a desk, a chair, and a window with curtains.
A wooden outdoor dining table set with glassware, candles, and lanterns, surrounded by lush greenery.

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Fairfield by Marriott Inn & Suites Key West at The Keys Collection
New Town
CA $199
CA $264 total
includes taxes & fees
Oct 14 - Oct 15
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.
A hotel room with a large bed, a TV mounted on a wooden cabinet, and a balcony with a view of palm trees.
A modern kitchen with a marble island, wooden cabinets, and pendant lighting.
A hotel room with a balcony, a bed, a desk, and two chairs.

Hampton Inn Key West FL

Hampton Inn Key West FL
Key West
CA $241
CA $272 total
includes taxes & fees
Oct 25 - Oct 26
Hampton Inn Key West FL
A wooden boardwalk with a palm tree and lamp post, leading to a waterfront.
A hotel room with a desk, two beds, a TV, a ceiling fan, and a balcony with curtains.
A pool area with lounge chairs, palm trees, and a building with a tiled roof.
A modern restaurant with a wooden counter, seating area, and large windows.

Courtyard by Marriott Key West Waterfront

Courtyard by Marriott Key West Waterfront
Northside Resort
CA $262
CA $295 total
includes taxes & fees
Oct 26 - Oct 27
Courtyard by Marriott Key West Waterfront
A swimming pool with lounge chairs and palm trees.
A bar area with a wooden counter, bar stools, and a sign that reads 'So we BEATON.'
A modern living room with a sectional sofa, a small round table, and a potted plant.
Sports facility

Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection
New Town
CA $175
CA $237 total
includes taxes & fees
Oct 25 - Oct 26
Hilton Garden Inn Key West / The Keys Collection
A hotel with a swimming pool, balconies, and a view of the sea.
A marina with jet skis docked in front of a hotel with a dock and a boat in the background.
A spacious bar area with a wooden counter and green bar stools, a seating area with a sofa and chairs, and a dining area with a table set for two.
A beach wedding setup with white chairs, a wooden arch, and lanterns.

Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
Key West Historic District
CA $344
CA $487 total
includes taxes & fees
Oct 26 - Oct 27
Hyatt Centric Key West Resort and Spa
A hotel room with a bed, a view of the beach, a hammock, and beach chairs.
A pool area with blue lounge chairs, a hot tub, and a covered seating area.
A marina with boats docked, a beach resort building, and palm trees.
A beachfront hotel with multiple colorful buildings, a pool area, and a boat dock.

Ibis Bay Beach Resort

Ibis Bay Beach Resort
Northside Resort
CA $159
CA $225 total
includes taxes & fees
Oct 14 - Oct 15
Ibis Bay Beach Resort
A balcony with a view of a pool area, palm trees, and outdoor seating.
A sign for Doubletree by Hilton Grand Key Resort surrounded by lush greenery and palm trees.
A hotel room with a bed, a desk, a chair, a balcony with a view, and a ceiling fan.
A conference room with a patterned carpet, multiple tables, chairs, and two chandeliers.

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
Key West
CA $182
CA $253 total
includes taxes & fees
Oct 27 - Oct 28
DoubleTree Resort by Hilton Grand Key - Key West
A swimming pool with water splashing, surrounded by palm trees and a building in the background.
A two-story yellow house with a porch, white railings, and green shutters.
The exterior of the Silver Palms Inn with a two-story structure, a green awning over the entrance, and a palm tree to the right.
A hotel with a pool, bicycles, and lush greenery.

Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West
CA $127
CA $239 total
includes taxes & fees
Oct 25 - Oct 26
Silver Palms Inn & Historic Homes
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Top Fleming Key Hotel Reviews

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent
"Staff was great"
Robert A 3-night trip
Posted 8 hours ago
DoubleTree Resort by Hilton Grand Key - Key West
Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"Being near the pool was very convenient. There was no A/C in the gym, the walk down the stairs from the balcony to the pool was hazardous. There was no walkway, just rocks. The elevators closest to our apartment was out of order which caused us to walk quite a bit. The floors in the apartment were very dirty. We requested to have them cleaned. They sent someone up while we were gone and they cleaned the apartment however the floors were left untouched. They didn't clean them. We advised the front desk, they apologized but it was never corrected. The shuttle was definitely a plus but get there super early because if there are 12 people before you, you're not going. The pool is beautiful and very clean. The food at the pool side bar was very good. So a lot of plus' but unfortunately some misses. The people at the front desk were always very friendly."
Helena 8-night trip
Posted 12 hours ago
Beachside Resort & Residences
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

8/10 Good
"Le déjeuner, le service de bar et l’accueil était top. L’attitude des femmes de ménage et la propreté des entretiens dans la chambre étaient très ordinaire."
Dominique 4-night trip
Posted 13 hours ago
Winslow's Bungalows - Key West Historic Inns
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

10/10 Excellent
"We loved this resort! We will definitely be returning here in the future. Great location- not far from Duvall St but close enough that it’s only a 10 minute drive."
Vernon 4-night trip
Posted 17 hours ago
Parrot Key Hotel & Villas
Havana Cabana at Key West

Havana Cabana at Key West

10/10 Excellent
"This was our second stay here. We love the low key vibe. The staff is always pleasant to deal with. The rooms are nice and the pool was well maintained. The food was great. All around great experience will be back again and again."
Jason T 7-night trip
Posted 19 hours ago
Havana Cabana at Key West
Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

10/10 Excellent
"Friendly Staff Nice Place"
Eric A 1-night trip
Posted 20 hours ago
Hilton Key West Resort & Marina
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"We went with 2 other couples 2nd year in a row at Southern Most, that should tell you how much we enjoyed it! Great location, food rooms were always cleaned."
Theresa 5-night trip
Posted 1 day ago
Southernmost Beach Resort and Guesthouses
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

8/10 Good
"Somewhat disappointed. Sink was stopped up on arrival, however it was repaired rather quickly. WiFi was non-existent. Room was very clean and staff was helpful. I would give it a 7 out of 10 for the price. I would stay again."
Barry 3-night trip
Posted 1 day ago
Hilton Garden Inn Key West / The Keys Collection
Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

8/10 Good
"Not applicable."
Nhia 2-night trip
Posted 2 days ago
Fairfield by Marriott Inn & Suites Key West at The Keys Collection

More cheap stays in Fleming Key

Ibis Bay Beach Resort

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL
CA $159
CA $225 total
Oct 14 - Oct 15
includes taxes & fees
Ibis Bay Beach Resort
Hampton Inn Key West FL

Hampton Inn Key West FL

3755 S Roosevelt Blvd Key West FL
CA $241
CA $272 total
Oct 25 - Oct 26
includes taxes & fees
Hampton Inn Key West FL
Southwinds Motel

Southwinds Motel

1321 Simonton Street Key West FL
CA $199
CA $272 total
Oct 14 - Oct 15
includes taxes & fees
8.6/10 Excellent! (1,385 reviews)
Southwinds Motel
Pegasus International Hotel

Pegasus International Hotel

501 Southard Street Key West FL
CA $187
CA $283 total
Oct 14 - Oct 15
includes taxes & fees
8.2/10 Very good! (1,001 reviews)
Pegasus International Hotel
Alexander Palms Court

Alexander Palms Court

715 South St Key West FL
CA $284
CA $320 total
Oct 14 - Oct 15
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
Alexander Palms Court
Tranquility Guest House

Tranquility Guest House

302 Angela st Key West FL
CA $177
CA $326 total
Oct 14 - Oct 15
includes taxes & fees
9/10 Wonderful! (35 reviews)
Tranquility Guest House

Hotels in Fleming Key with star rating

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